Geranyl pyrophosphate

Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many thousands of natural products.^[1]

Geranyl pyrophosphate

Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name (2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate
Identifiers
CAS Number	763-10-0 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17211 Y
ChEMBL	ChEMBL41342 Y
ChemSpider	393471 Y
DrugBank	DB02552 Y
IUPHAR/BPS	3051
MeSH	Geranyl+pyrophosphate
PubChem CID	445995
CompTox Dashboard (EPA)	DTXSID801315430
InChI InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+ Y Key: GVVPGTZRZFNKDS-JXMROGBWSA-N Y InChI=1/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+ Key: GVVPGTZRZFNKDS-JXMROGBWBE
SMILES O=P(O)(O)OP(=O)(OC/C=C(/CC\C=C(/C)C)C)O
Properties
Chemical formula	C10H17O7P2
Molar mass	311.19
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Occurrence

GPP is an intermediate in the isoprenoid biosynthesis pathway that produces longer prenyl chains such as farnesyl pyrophosphate and geranylgeranyl pyrophosphate as well as many terpenes.^[2] It can be prepared in the laboratory from geraniol.^[3]

Isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) are condensed by geranyl pyrophosphate synthase (dimethylallyltranstransferase) to produce geranyl pyrophosphate (GPP) and pyrophosphate. The carbon skeletons of DMAPP and IPP have been colored to indicate their location in GPP.

Microbial toxicity

Intracellularly produced GPP has been shown to be toxic to the bacteria E. coli at moderate doses.^[4]

Related compounds

• Geraniol
• Farnesyl pyrophosphate
• Geranylgeranyl pyrophosphate

See also

• Dimethylallyltranstransferase